HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisobutylamine → (S)-1-(N,N-Diisobutylamino)-2-[3-(2-benzyloxy-1-methylethyl)-2-(3,5-dimethylphenyl)-1H-pyrrolo [2,3-b]pyridin-5-yl]-2-methylpropan-1-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisobutylamine | HCID 8085 | — |
| Reactant | PyBOP | HCID 2724699 | — |
| Reactant | (S)-2-[3-(2-Benzyloxy-1-methylethyl)-2-(3,5-dimethyl-phenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-2-methylpropanoic acid | HCID 15887219 | — |
| Reactant | Sodium chloride dihydrate | HCID 23713072 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Triethylamine | HCID 8471 | — |
| Product | (S)-1-(N,N-Diisobutylamino)-2-[3-(2-benzyloxy-1-methylethyl)-2-(3,5-dimethylphenyl)-1H-pyrrolo [2,3-b]pyridin-5-yl]-2-methylpropan-1-one | HCID 15887220 | — |
Reaction Steps
PyBOP is added to a stirred mixture of (S)-2-[3-(2-benzyloxy-1-methylethyl)-2-(3,5-dimethylphenyl)-1H-pyrrolo [2,3-b]pyridin-5-yl]-2-methylpropanoic acid, diisobutylamine and triethylamine in CH2Cl2 at ambient temperature. After approximately 12 h, the reaction mixture is poured into water/brine (1:1) and extracted with ethyl acetate. The combined organic extract is washed with brine, dried (MgSO4) and concentrated in vacuo. The residue is purified by flash chromatography on silica gel (gradient elution; 60-75% ethyl acetate/hexanes as eluent) to give the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06025366 |
| Source dataset | uspto-grants-2000_02 |
| ORD ID | ord-a884ccdc4be94cedaee4346e44189695 |
| Source note | uspto-grants-2000_02 |